Enantiopure fluorous 1,2-diaryl-1,2-diaminoethanes: synthesis and applications in asymmetric organometallic catalysis

Abstract

The synthesis of a new enantiopure fluorous 1,2-diaryl-1,2-diaminoethane bearing two fluorous ponytails is described. The palladium-catalyzed reaction of 1,3-diphenyl-2-propenyl acetate with dimethyl malonate in the presence of this ligand and its analogue bearing four fluorous ponytails gave the alkylated product with ee up to 44%. Their application as ligands in hydrogen transfer reactions associated with rhodium, iridium, or ruthenium in a two-phase system gave ee up to 39%, the catalyst being recycled without loss of enantioselectivity in the case of the ruthenium complex.